Red-orange monoazo dye and process of making same.



- 20 whatever be the particular manner in which the UNITED snares. P T NT OFFICE.

.WI L HELM HERZBERG, or BERLIN, AND osoAR SPENGLEB, 'OF NI'EDER-SCHQN-WEIDE, in. BERLIN,.GERMANY, ASSIGNORS TO AGTIEN GESELL'SGH'AFTFUR ANILINFABRIKAT N.

OF BERLIN, GERMANY.

i No; 865,587.

I hpplicationfileil October 26,

, To aitgwhom it may concemf Be it known that we, WILHnLM HERZBERG and Os- CAR SPENGLER, residing, respectively, at Berlin, Hagelsbergerst-r. 10, and Nieder-Schiinweide, near Berlin, in the Kingdom of Prussia, German Empire, have invented newand useful Improvements in new Red-Orange Mo'noazo Dyestuffs and Processes of Making Same and we do hereby declare that the following is'a full, clear, and exact description thereof; which will enable others skilled in the art to which it appertains' to make and use the same. I Our present invention relates to the manufacture of a new monoazo-dyestuff which maybe obtained by diazotizing and then combiningortho-chloro-para-ni- 'itranilin with beta-naphthcl it having been found that the product resulting from this azo-combination is distinguished by its very clear 'and brilliant red-orange tint and by anextremelygreatfastness to light, These advantageous qualities of the new product are present dyestufi is made. For. instance, when producing the dyestuff on a piece of cotton cloth, which manufacture occurs, generally speaking in-the manner usual for the production of para-nitranilin red, there is obtained a clear brilliant red orange tint the fastness of. which to light is much greater than that of p ara-nitranilin-red. On the other hand the dyestufii? may be produced for instance in the presence of a substratum or of-other suitable substances such as are used in the production of color-lakes, like aluininium' hydroxid or a/ barium or calcium salt. In this case also the dyestuff or ,the lake respectively thus produced showa very 'cle ar and bril- "liant-red-orange tint possessing-a very. great iastness to light; furthermore the lakes thus obtained are insolu- 3 5 ble in water and practically insoluble in alcohol and in oil. They are most adapted for chromolithography as well as for paper-staining and for wall-paper printing. vThe following examples may serve to illustrate our invention, the parts being by weight:

Example 1: '15 parts of beta-naphthol are dissolved in a suitable quantity of water by means of the calcu- Y lated quantity of caust c soda; this solution 15 feebly acidulated with hydrochloric acid the beta-naphthol being thereby precipitated in a very fine distribution. To this mass is added while stirring well a diaz'o-solution of ortho-chloro-para-nitranilin which is prepared from 17,2 parts of this base by means oi 7 parts of sodium nitrite and 35 parts of hydrochloric acid (20 Baum specific gravity). Combination immediately occurs and is complete within a short time. The mass having been warmed on a water-bath it is filtered, washed and dried. Thus is obtained a clear red-orange powder of'great brilliancy which is insoluble in water Specification of L tters Patent.

. lution which solution on addition oi ice precipitates ner by means of 7 parts-of sodium nitrite and of 35 [BED-ORANGE MONOAZO DYE AND rnoonss OF MAKING-SAME.

Patented Sept. 10., 1907. I 1906. Serislhlo.34=0,690.

and in an aqueous solution of an alkali'or of. an acid; it dissolves in concentrated sulfuric acid to a violet soreil flakes. The dycstuff dissolves in analcoholic solution of caustic soda with a red coloration possessing a castto violet. By the action of a strong reducing agent the dyes'tuff is split up-yieliiing 'ortho-chloropara-nitranilin besides 1.2-a1i1idonaphthol. It is convenient; to say that the dyestuff shows its greatest brilliancy when the combination occurs in a solution the acid reaction of which is due to hydrochloric acid, but the production, may also'be performed in an aceticacid solution or in alkaline solution.

Example 2: Production of the new azo-dyestujj" in thr prese'n'ce'ofo suitable Zake-s'ubstratum.-17,2 parts oi-a ch-loro-para-nitranilin are diazotized in the usual man parts of hydrochloric, acid of 20 Baum specific gravity. The diazo solution'thus obtained is'diluted with waterup to about 500 parts and then added with 100 parts of an aqueous solution bi barium-chlorid con: taining 20 per cent. of this salt. On the other hand there is prepared a solution 0t 14 parts of beta-naphthol in 600 parts of water by means'oi 10 parts of causticsoda -lye (40 Baum specific gravity); to this 'solutionare added while stirring well 1,000 parts of a freshly prepared paste of aluminium hydroxid (containing 5 per cent. of thishydrate) as well as 20- partsoifinely pulverized barium sulfate. Now the diaio-s'olutio n as above prepared is allowed to run into the beta-naphthol preparation. while stirring well." (iombinationoccurs immediately, a clear and brilliant red-orange color-lake being formed; the reaction is complete within ashort time. The mass is thenfiltered, washed and dried. The -color-l ake thus'produced is a clear red-orange powder of great brilliancy, which is insoluble inwater and practically insoluble in alcohol and 90, oil. It is most adapted for chrdmolith'ography as wellas for paper-staining and for wall-paper printing.

It is obvious to those skilled in the art that the present} invention is not limited to the foregoing examples nor to the details given therein. First in applying the production of the new dyestuff to the manufacture of azo-colors'on a vegetable fiber as for instance on cotton or on a vegetable fiber other than cotton the special conditions in every case are tobe taken so as to suit the special kinder the respective vegetable fiber; Example 1 may therefore be varied within wide limits and may be-adaptcd to the production of 'az'o-colors on vegetable fiber without departing from the scope of the present invention. Furthermore .when producing the new azo-dye in'the presence of a lake substratum or lake substrata any other suitable substances such as jarr- 'useclin the production of color lakes may be used instead of the 'respectiveingreclientsused in Example 2; also in this way there maybe taken variations within wide limits Without] departing from the scope of the;

present invention v is obvious that the (lyestuff may also be produced first without the presence oi such a substratum or 1 lake forming salt or compound'and then precipitated on such a substratum or the like, as this is another method usual in the manufacture of color lakes.

Having now described our invention and the manner tin which the same is to-he carried out what We 1. The process of producing e. red-orange-monoazo-dyestuil'. which process consists in diazotizing ortho-chloro-- tinguished by its brilliancy and by a very great fastnessl coloration which solution on the addition of ice precipisred flakes. this dyestutt eing soluble in an alcoholic solution of caustic soda with a red coloration possessing a castito violet and yielding" by treatment with strong reducingvagents ortho-chloro-para-nitranilin besides 1.2411111- donaph'thol, and which dyestufl when the combination of the diam-compound of ortho'chloro-para-nitranilin with beta'na "hrh'oi occurs in the presence of barium-chlorid toguthei with aluminium-hydroxid and barium-sulfate forms a clear i'edoran ge colored powder of great brilliancy, which powder is insoluble in water-,and practically insoluble in Alcohol and in oil. v I

Injw'itness whereof we have hereunto signed our name this 8 day of October-Q1906. in the presence of two subscrihing witnesses I 1 WILHELM HERZBERG.

OSCAR SI'ENGLERi Witnesses HENRY HASI'EIR, I Town UAR Il um. 

